Jamie Rellis (Kunis) is a headhunter ("I prefer corporate recruiter") who lures Dylan Harper (Timberlake), a website art director, to New York to interview for GQ. He takes the job and the pair become close friends, eventually agreeing to have sex — just sex, with no further attachment — while they're on a break from romance. They both go through a few other people in the film and deal with issues surrounding their parents.

This film provides examples of:

Affectionate Parody: The two leads mock many conventions of traditional romantic comedies and even when Dylan stages a 'movie like reconciliation at the climax' he says how impractical it is in real life. The movie still follows the same format and ends the same way.

Ambiguously Brown: Jamie. Justified as her mother cannot remember what ethnicity her absentee father was; possibilities include Greek, Russian, Hispanic and Middle-Eastern. note In case you're curious, Mila Kunis was born in Ukraine to Jewish parents.

Idealized Sex: Averted at first: there's a lot of direction and negative reactions, and Dylan has to stop once because he has to pee. Played straight later, when Dylan and Jamie have sex during the visit to Dylan's family.

Jizzed in My Pants: Dylan jokes about it. He mentions that he sneezes when he has an orgasm; later, when he's making out with Jamie, he sneezes in her face.

Jamie: Really? Already?

Dylan: Just kidding.

Missing Mom: Dylan's mother left his father 10 years before the movie.

Mood Whiplash: It's all frothy fun and games and witty repartee, until Dylan's dad, who is suffering from Alzheimer's, is introduced. Then the scene dives straight into awkward and heartbreaking.

The Mountains of Illinois: Parodied in the film-within-a-film Jamie and Dylan watch. The characters are riding in a horse-drawn carriage, pointing out New York landmarks with rows of obvious palm trees visible in the background. Also from said film, Los Angeles Union Station representing Grand Central Terminal.

Averted by the movie itself in that all scenes were shot in either New York City or Los Angeles. However the interior of the New York GQ offices were a set in LA and although they were in NY, the Empire State Building behind Jamie in the opening scene was digitally painted in. This was also the first movie that actors were allowed on the actual Hollywood Sign.

Mistaken for Gay: Tommy assumes Dylan is gay when they first meet, and keeps asking Dylan if he is sure that he's not gay.

Not Staying for Breakfast: Parker, the guy who Jamie starts dating after her she and Dylan stop having sex attempts to do this. Unfortunately for him, Jamie wakes up before him, and catches him on the street.

Dylan insists that "Closing Time" is by Third Eye Blind, until the final scene when he finds out it's actually Semisonic.

Also Jamie blinks when she curses, and Dylan talks about how modern planes "practically land themselves" everytime he is on a plane. In a later scene this is shown to have been picked up from his father.

Shout-Out: Jamie's mother changes the nationality of Jamie's fatherthroughout the movie. At one point the mother mentions a lover, who reminded her of her daughter's father, having a "Cold War" accent. Mila Kunis was born in the former Soviet Union.

Shower of Love: In a deleted scene, Jamie and Dylan have sex in the shower. Dylan complains that Jamie is wearing a shower cap (because she just got her hair done).

Smells Sexy: Hilarious for the audience, incredibly creepy for Dylan when he tries to sleep with someone other than Jamie.

At the beginning, after Jamie's boyfriend broke up with her, she says: "I really have to stop buying into this bullshit Hollywood cliché of true love. (sees a poster for The Ugly Truth) Shut up, Katherine Heigl, you stupid liar!"

Dylan's girlfriend breaks up with him right before they're supposed to go to a John Mayer concert. He remarks: "Thank you for doing this before the concert, by the way. Best breakup ever." Later, when he mentions to Jamie that his ex-girlfriend loves John Mayer, she pretends to retch.

After Dylan and Jamie end their "friends with benefits" arrangement, they go out for a walk and both try to pick up someone. Dylan notes that the woman he noticed is reading a book. Jamie responds: "It's probably Nicholas Sparks."

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